


May The Best Man Win

by Writerofshit (kay_samm)



Category: Rooster Teeth/Achievement Hunter RPF
Genre: GTA AU, Hitman/Bodyguard AU, M/M
Language: English
Status: In-Progress
Published: 2020-06-16
Updated: 2020-08-01
Packaged: 2021-03-04 04:54:01
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 11,770
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24747901
Author URL: https://archiveofourown.org/users/kay_samm/pseuds/Writerofshit
Summary: If someone has a hitman after them, but hires a bodyguard, their life depends on who's better at their job.Or: Jeremy sincerely hopes he's a better hitman than The Vagabond is bodyguard.
Relationships: Gavin Free/Michael Jones, Jeremy Dooley/Ryan Haywood
Comments: 27
Kudos: 92





	1. Chapter 1

**Author's Note:**

> I saw a post on Tumblr with this premise, and I just couldn't help myself. Shoutout to Just-shower-thoughts, a blog that is literally just reposts from reddit.

Jeremy has decided he no longer wants to make deals in bars. He’s almost never sure who exactly his client is going to be, he’s far too tempted to get absolutely plastered after the deal is done (when in Rome, you know?) and he always feels awkward looking at photos of someone who’s going to end up dead. At least in public he does. It’s never come back to bite him in the ass, but still. He worries.

Tonight he’s lucky, to some degree, because clearly the sketchy guy in the trenchcoat, glancing around like he’s worried _he’s_ going to get taken out, is the client. Jeremy guesses he wants some politician dead, or maybe somebody from an opposing company. He reads corporate for sure. Those hits tend to leave a bad taste in his mouth. Can’t they just have a corporate dick measuring contest and call it a day? Why do they need to bring murder into it?

But whatever. If he gets paid he gets paid.

Jeremy waves the guy over, wanting to get this part over with. The longer he sits at this bar, the more whiskey-cokes he’s going to drink, the more agreeable to lower prices he’ll be. He needs to be reasonably sober in order to be reasonably firm.

“Uh. Hi.” The guy says by way of greeting, giving Jeremy an obvious once-over. “Are you-uh, the guy?”

Jeremy raises an eyebrow. Based on that alone he’s not sure he wants to murder _anyone_ on this guy’s behalf. “Depends what you’re looking for.” He says with a smirk and yeah, he could stand to be less flirty, but he definitely doesn’t work for him if he takes offense.

“Um.” The guy reaches into his coat, producing a slim manila folder. Jesus Christ, could he be more cliche? “This kind?”

Jeremy grins, because despite it all, at least the guy is prepared. He leans in conspiratorially, dropping his voice to barely more than a whisper. “You mean the kind that kills people in little folders like that?” he leans back. “Could be, depending on the price.” Which is mostly true. For all his worry about being too drunk to negotiate, he’ll admit he’s been a little strapped for cash as of late, so he might be willing to make a bit of a compromise.

“Uh. I heard your going rate… well it’s in here.” He gestures with the folder. Trenchcoat glances around again, and the anxiety this guy is oozing is starting to be a bit grating. Jeremy is about to agree to anything just to get this fuck away from him. Any money is good money at this point.

Even though he doesn’t fully hold out the file, Jeremy reaches forward and snatches it from his hand anyway. He cracks it open briefly, looking mostly for a dollar sign. That’s… twice his going rate, actually, but he’s not about to let this guy know it. He’s going to take what he can get and do so quietly. He catches the name, and _oh_.

Isn’t that wonderful.

He doesn’t let on to the man in front of him though. Just snaps the file closed and nods. “Alright, sounds like a plan dude.” Jeremy hops off the bar stool and claps the guy on the shoulder. “I’ll keep you posted if anything changes.”

Trenchcoat looks surprised.”But you- you don’t have my number.”

Jeremy grins. “Buddy, if I didn’t know how to track people down when I needed them, I’d be real shit at my job.”

The guy raises an eyebrow, but doesn’t say anything.

“And I assure you. I’m _excellent_ at what I do.” 

\---

A few minutes later, he’s back in his car, driving toward his apartment. He glances at the file in the passenger seat, considers the photo and the name and the whole job he’d just signed up for. He thinks about the promise he’d just made.

_Fuck._

It isn’t like he’s never killed someone he’s known. It’s bound to happen here and there, and besides, most of the people he knows probably deserve it anyway. This time though… he doesn’t know the guy personally. They’ve met a handful of times at events, shit he hates going to but his new target always seems to get a kick out of. Guy is a bit of a prick, and there are probably hundreds of people in the city who wouldn’t mind seeing his head on a stake. Jeremy’s fairly indifferent about it.

Or, he would be, if he didn’t happen to know one of his target’s best friends.

He sits in the parking garage a moment before he heads up, dialing a number on his phone. Money is money, yeah, but he feels a little guilty not giving his friend a heads up. He’s not completely heartless.

The phone picks up on the third ring.

“ _Yo. The fuck you want?”_

“Michael? We may have a problem.”

\---

“I can’t believe you agreed to this.”

It’s been less than an hour since he’d called Michael, and now he’s here, in Jeremy’s apartment, hands on his hips, looking less like a man hearing that there’s hit out on his best friend and more like a disappointed mother.

“What was I supposed to say, Michael?” he says, even though the answer is exceptionally clear.

“You say _no,_ Jeremy, _no I won’t murder a friend of mine, actually.”_

“He’s not my friend, he’s yours.” Like it matters.

“Oh yeah, that makes it so much better, really.” Michael throws his hands up in the air, clearly exasperated. Jeremy can’t really blame him.

“Look, this is why I’m telling you.” It is, admittedly, not the smartest plan he’s ever come up with. It’s only making his job harder, in fact. But he figures the challenge of it all will make them both rest easier, in the end. “This way you can let him know or whatever, and if he wants he can fuck off somewhere.”

“And then what, Jeremy? You track him down and kill him in some shithole hotel room in the middle of bumfuck nowhere? You wait for him to think he’s in the clear, he comes back and you fucking off him in his apartment?” Michael throws himself across the couch across from Jeremy, looking up at the ceiling. “I really don’t know what the fucking endgame is here.”

Jeremy sighs. Maybe it’s a mistake, letting Michael in on this. It’s only adding to the guilt he already feels.

“I don’t… know either, honestly.”

Michael sits up ever so slightly to meet his eyes.”Don’t kill my best friend, man. It’s a really shitty thing to do.” 

Well. He’s not wrong.

“It’s a _job,_ Michael. It’s literally just what I do for a living.”

Michael snorts. “Pun intended, I’m sure.”

Jeremy pauses. Huh. Hadn’t even registered to him. “Seriously. If it were damn near anyone else you wouldn’t care. Fuck, dude, how many hits have you actually helped me out on? You weren’t begging me not to kill them. How is this any different?” 

And yeah, he knows his argument is flawed. It’s one thing to hear about your friend killing some stranger over something they probably deserved. It’s something else entirely to know that your friend has apparently been hired to kill one of the only people in the world that you’re close to.

“Oh fuck off, Jeremy. If it were damn near anyone else you wouldn’t have bothered to warn me.” Now he’s waving a finger at Jeremy, really driving home the disappointed mother approach he’s taken. “You fucking know it’s different.”

“Look, man,” Jeremy says, leaning back in his chair, hands behind his head. “I think I’m gonna do what I gotta do. But I’m giving you the opportunity to warn him. To try and protect him.” He shrugs. “To my own detriment, might I add.”

Michael laughs, dry and humorless.”You’re a real asshole sometimes, you know that?”

“Michael! That hurts!” Jeremy grins at him, “Only sometimes?”

This time when he laughs, there’s a little bit of merit to it.

"Fuck you." Michael stands, crossing his arms. “Guess I better go warn the dipshit. I’m guessing you’ll start working tomorrow?”

Jeremy shrugs. “Eh, working on tracking him down, yeah. Knowing what I do about him, I’d say it’ll be a week or so before I actually find his apartment. So take that for what it’s worth, I guess.”

“Right. I’ll keep that in mind.” Michael says, pulling his jacket on. “I guess I’ll see you around, Jeremy.”

“I’ll see you. May the best man win.”

“Ha. Guess we’re both fucked, then.”

With that, Michael leaves, closing the door gently behind himself.

Meanwhile, Jeremy just wonders what the fuck he’s gotten himself into.


	2. Chapter 2

**Notes for the Chapter:**

> I didn't mention this last time, but each chapter is a different person's POV, mostly because I like jumping around like that. My personal favorite happens to be Michael, because, as you'll see, he's the only one who responds close to a normal person, I'd say.

“So someone really wants me dead that badly, hmm?”

This is not the response Michael had been expecting. At the worst, crying and freaking out. At the least maybe a little bit of fear. But Gavin seems altogether unfazed by this development.

“Yeah, that would be the major plot point here.”

“Well. That’s not the best news I’ve ever heard.” Gavin says, pulling one of his cats into his lap. He’s staring off into the distance thoughtfully. “No, that’s quite bad actually, isn’t it?”

“No shit, Sherlock.”

“Suppose it had to happen eventually.” Gavin says with a shrug.

“ _Gavin._ Can you act like you care about this at all?" Michael says. He's really taken aback by this nonchalant attitude Gavin has. "The whole reason I came over here was to warn you, I thought-”

“How’d you find out, Michael-boi?” Gavin turns his eyes on him, watching Michael intently.

“I-” He falters, unsure if he should reveal his source on this one. It’s a little shitty to tell your boyfriend that one of your only other friends is planning on killing him.

Also shitty of a friend to kill another friend’s boyfriend, so. _Fuck Jeremy,_ Michael thinks.

“The guy who took the job is a friend of mine.” Michael confesses. He doesn’t want to be overly specific, and what he’s said is honest enough.

“Hmm.” Gavin tilts his head, still far too calm about the whole situation. “Friend who knows about you and me, or-?”

“No.” Michael says honestly. “He doesn’t know about us, just...that we’re close. Friends.” he tacks on, because normally Gavin would run with that, turn it into an innuendo.

Not this time.

“Right. So- It’s Jeremy then?” Gavin says with a smile.

“How the fuck.” It’s less of a question and more of a confirmation. It’s honestly not that hard to figure out.

“Come on, Michael. You have approximately three friends besides me, only two of whom would actually accept a job like this, and Ryan is well aware of our relationship.” Gavin grins at him wolfishly. “Doesn’t leave a lot of options.”

“First of all, fucking rude. I have more than three friends, thank you very much. And second, fuck you. I’m out here trying to save your sorry ass-”

Gavin waves a hand dismissively. “Please. I just texted Ryan, he said he’s willing to keep an eye on me until this blows over.”

“Because murder for hire often just _blows over,_ right,” Michael says, rolling his eyes.

"In this city?" Gavin shakes his head, a small rueful smile playing at his lips. "Everything blows over eventually."

He has a point, Michael knows, but he also can't help himself from worrying about this whole thing. He's known Jeremy for a good minute here, knows his going rate isn't exactly cheap. Anyone willing to pay that much for someone's demise certainly means it. Certainly isn’t going to give up too easily. 

Not for the first time, he wonders why Gavin isn't taking this seriously. He knows the brit has always been laid back, always too relaxed for his own good. Michael can count on one hand the number of times he's seen Gav get genuinely riled up over something. Sure, he was often obnoxious about… mostly everything, really, but there was never any sincerity to him.

“Gav, do you think it might be a good idea to get out of her awhile? Head south, maybe.” Michael chuckles, but there’s no real humor to it. “You always did like Florida.”

Gavin narrows his eyes.”You want me to just run away from this?” his voice is sharp, daring Michael to deny it. Despite his harsh tone, he leans down, sets the cat gently on the floor. He pulls his knees to his chest. “Would you be running, Michael?”

Michael kneels in front of him on the couch, reaching out for his hands. “It’s not running, it’s- think of it as a conveniently timed vacation. It’s not like we don’t deserve one.”

“I can’t just pick up and leave, Michael.” He looks down at their hands, tangled together. “You know I have work to do.”

“Fuck your work to do.” Michael pushes forward, crowding into his personal space. He pulls his hands from Gavin’s to move them to his face, thumbs brushing along his cheekbones. “Whatever you’re working on is not worth your life.”

“Don’t you have a job too?” Gavin won’t meet his eyes.”I’m sure Geoff mentioned-”

“Fuck Geoff too. He’ll make it without me for a couple of months.” He slips his hands to Gavin’s neck, pulling him forward gently, their foreheads colliding. “Just come with me. We’ll do it together.”

“Michael, I-” Gavin falters, shutting his eyes tightly. “I trust Ryan, alright? He’s not going to let anything happen to me.” He opens his eyes again, but they’re focused on Michael’s nose. “Don’t you trust him?”

“Yeah, I do. But,” he breaks their contact, hooking Gavin’s chin with one finger, forcing their eyes to meet. “I also trust _Jeremy,_ Gav. I can’t say I’ve ever seen him miss.”

Gavin smiles weakly. “There’s always a first time for everything, isn’t there?”

Michael sighs. “Yeah, but who’s it going to be? Ryan or Jeremy?”

Gavin’s smile disappears. “It’s going to be _fine,_ Michael. I know it will.”

Michael only shakes his head, sitting back on his heels. “Gav-”

“Are you staying tonight, Michael?” Gavin looks at him hopefully, all wide eyed and innocent.A far cry from the quiet seriousness he’d had since Michael told him of the situation.

Michael reaches out for his hands again, rubbing circles with his thumb into the back of Gavin’s hand. “Do you want me to stay?”

“I mean, you’re all hell bent on protecting me. Seems like a pretty ideal way.” He smiles, but the way he worries his bottom lip belies his nerves.

“Yeah.” he takes a deep breath, “Yeah, you’re right.”

Gavin is studying him, and Michael can’t help but shiver under the scrutiny. He’s always been an open book to Gavin, and, for the most part, Gavin has been the same to him. When they first got to know each other, yeah, Gavin wouldn’t give him an inch he didn’t beg for. But through time and repeatedly proving himself as someone who was never going to walk away, who would head into any battle on his behalf, who never planned on making it out if they weren’t doing it together, Michael won him over. For years now, they have remained the one constant for one another. 

There is no Gavin without Michael beside him.

There is no Michael without Gavin to come home to.

“Come on.” Michel says, pulling him gently by the hand. “Let’s go to bed”

\---

It feels as if he’s no sooner asleep before he’s woken up by a voice.

“You two are going to get yourselves killed.”

“Jesus fucking Christ!” he can’t himself. It’s his go-to when startled.

“Oh calm down. It’s just me.” Ryan says, gesturing at himself.

“My bad, you’re right, I should expect to wake up to tall dark and fucking terrifying two inches from my face. Of course.” Michael says shortly, reaching for the bedside lamp. It clicks on, bathing the room in harsh yellow light.

“There’s a hit out on your boyfriend. You probably shouldn’t be asleep at all.” Ryan says darkly.

“Fuck, dude, you can’t just _do_ this shit. I could have had a fucking heart attack.” Michael says, sitting up against the headboard. He glances to his left, to Gavin. Despite the commotion, he’s snoring peacefully. “Is he still fucking sleeping? _Seriously?”_ He shakes his shoulder roughly. “Gavin. Wake up” he glances up. “Ryan’s here to scare the shit out of us.”

Gavin blinks up at him “Hmm?” he squints. “Ryan? What are you doing here?” He rolls into Michael, arm around his waist and head in his lap. Michael wraps an arm around his shoulders. His heart is still racing.

Ryan leans in again, always serious. “The three of us need to have a conversation.” He says. Serious, but also a dramatic fuck.

“Only if you lose the creepy fucking mask. I fucking hate that thing.” Michael says, rolling his eyes.

“It’s a very important part of the ensemble, Michael.” and he can hear the pout in his voice.

“Yeah, well, it’s a starring role in my fucking nightmares and I don’t need it in my goddamn face right now.” From the moment Ryan had granted them the privilege of seeing his face, Michael has been adamant that he never wear it around them. 

Ryan _‘hmphs’_ but takes the mask off.

“Serious question, Ry, do you go _anywhere_ without that shit on your head?” it's been years of protesting, and it never really worked anyway.

“Grocery stores, usually.”

“ _Usually._ ” Michael repeats sarcastically. “Fantastic. Remind me to hold any further meetings at the Whole Foods.

“Michael. I do have a reason for being here.” Ryan says, sitting himself at the food of their bed. Michael decides against making a guard dog joke, but it’s on the tip of his tongue. “We really should get to it before he falls asleep again.” he nods at Gavin, whose eyelids are fluttering.

“ m’awake” he says unconvincingly.

“My mistake.” Ryan says dryly. “Clearly you’re completely focused on the task at hand.”

“Gav.” Michael says, poking him in the cheek, “Come on, sit up.”

Gavin grumbles, but does as requested, still curling up to Michael, head on his shoulder.”I’m _up,_ god. Since when do you two ever want to talk to me this badly?”

“I’ve done some research.” Ryan says instead of answering. “Into this whole, you know, somebody being hired to kill you thing? That little annoyance that seems to have popped up?”

“Yeah yeah, we’re aware.” Gavin says. “What about it?”

“Your hitman is named Jeremy Dooley.” Ryan says matter-of-factly, and Michael fights the urge to react. “From what I can find, this isn’t exactly his first rodeo. Which is, of course, not the best news for us.”

“Alright, great.” Michael says quickly, “but what’s this mean for Gavin? What’s he supposed to be doing?”

Ryan cocks his head, clearly confused by the dismissal. “Well, ideally he’d get the hell out of here-”

“Gavin, I told you we-”

“ _Alone._ ” Ryan finishes, as though Michael hadn't been speaking.

“Why would he go alone?” Michael asks, immediately defensive. “I would think it’d be best for him and I to go, leave you here to… research, or track, or whatever it is you do.”

“Obviously not completely alone, I would go with him.” Ryan says, like it's the simplest thing in the goddamn world.

“How is that different to what I’m saying?” because he'll be damned if he's going to let this actually happen.

Ryan pauses, seeming debate his next words. “Well, no offense, but I would clearly have better odds defending him than you would-”

“Fucking _rude,_ and also _bullshit-”_

“And honestly, you would be better at finding out information. You have more connections that won’t raise questions.” Ryan says with a shrug.

“Who gives a shit about raising questions? No, I’ll get him out of here, we’ll go south somewhere, probably.” Michael smirks. “It’ll be like a cute little couple’s getaway.”

“Can you guys maybe not talk about me like I’m not here?” Gavin says, rolling his eyes. “You can argue about this all night, but it’s pointless. I’m not going anywhere.”

“Gavin-”

“No, Ryan.” Gavin says, and Michael is surprised by the edge of finality in his voice. It’s not often that Gavin is the one to put his foot down about something. In fairness, it is his life on the line, no one else’s. “If you do your job correctly, I won’t actually be in danger.”

Ryan raises an eyebrow. “If?” he repeats, clearly offended.

Michael rolls his eyes. This is neither the time nor place for bickering about Ryan’s track record.

“Look, if he really doesn’t want to go, it’s not like we can force him, Ryan.”

“I beg to differ.” Ryan says darkly.

“No.” Michael says with a sigh. “It’s up to you, Gav.” He rubs his shoulder gently, squeezing him a little bit closer. “I think we should leave, yeah, but if that’s really not what you want, then I guess we stay.”

“Thank you.” Gavin says softly, tilting his head to kiss Michael. It’s soft and gentle and shouldn’t feel as bittersweet as it does.

Ryan clears his throat. “Michael. Could I speak to you privately for a moment?”

“Anything you’re going to say to him you can say here.” Gavin says, not giving Michael a chance to answer. There’s a twinge of annoyance to his voice. “It’s not like he won’t tell me anyway.”

Ryan purses his lips.”Hmm. While that is a lovely sentiment,” he stands, turning toward the door. “I’m sure you’re eager to get back to your beauty sleep.” He doesn’t wait for a response, walking out and leaving the door open behind himself. The implication being that Michael will obviously follow.

Michael lets out a breath he hadn't realized he’d been holding. “I- I guess I’ll go talk to him.”

Gavin sighs, but pulls away, scooting so he’s lying down again. “Alright. I’ll be here, I guess.” he smirks up at Michael. “I hope, at least.”

“Not funny.” He leans down to kiss Gavin on the forehead before following Ryan.

\---

“Alright, what’s the big secret here, Ryan?” Michael asks, sitting on the couch. Ryan is standing in the middle of the living room, mask on again. That’s not creepy as fuck, no. “You wanna know what to get him for Christmas, or what?”

“I think it would be best if you left, Michael.”

“Shit, no foreplay at all?" He jokes, but there's no laughter to pair with it. "Just straight into kicking me out?”

“Michael-”

“I mean, my answer is no, obviously. If Gav’s not leaving then neither am I.” he crosses his arms, even though hes sure it just makes him look like a petulant child.

“I’m not telling you to leave the state, or even the city.” Ryan says. “But I don’t think you should around Gavin, for the time being.”

“And why the fuck not?” A petulant child with the mouth of a sailor, then.

“The more known associates Gavin has around him-”

“ _Known associates._ ” Michael repeats mockingly, “Fuck off. He’s my goddamn boyfriend, and I’m not going to leave him alone.”

“You understand that by coming and going as you please, it’s that much easier to simply track you. A very obvious trail that leads straight to Gavin. You’re a liability.” Ryan crosses his arms, apparently attempting to stand his ground on this issue. He comes across far more badass with it, to be fair.

Well too fucking bad.

“Who says I plan on going anywhere? I’ll stay here with him. Hell, I’ll probably keep him from going stir crazy.” He’s not lying. If Gavin agrees to at least stay put in the apartment, it won’t be long before he gets restless.

“I was able to get into this apartment, into your bedroom, inches from the both of you, and you had no idea." Ryan shakes his head. "If I was the one trying to kill Gav you’d both be dead right now. You wouldn’t have even woken up.” 

“Glad you’re on our side then.” Michael says, even though he’s not sure he actually is right now.

“ _Lucky_ I’m on your side.” Ryan corrects him. “You’re not protecting him by being here.”

“I’ll step up my security detail, don’t worry.” Michael says, standing. He doesn’t need this shit. “Is that all you wanted? To tell me why I’m a shitty boyfriend? You wanna tell me why my parents are disappointed in me while you’re at it?”

There’s a beat of silence, and Michael gestures to him as if waving him forward. “Anything else?”

“I did have more to discuss with you, yeah.” Ryan says with a sigh.

“Fucking fantastic.” Michael says, falling back onto the couch.”This day just gets better and better.”

“Gavin has told me, in the past, that you have a ...good friend, someone you’ve helped out here and there. Named, coincidentally, Jeremy.” Ryan pauses, like he's waiting for a confession.

Michael swallows. He had been hoping to avoid telling Ryan that it was his friend who was after Gavin. He already thought Michael’s mere presence was putting Gavin in danger, that little tidbit of information was not going to help his case.

“What are you getting at, Ryan?” Michael asks, even though he obviously knows.

“Come on, Michael. Just be honest.”

It takes everything in him not to tell Ryan to fuck off with his interrogation techniques, they aren’t going to work. Instead he settles for sort of honesty.

“I can’t imagine my Jeremy coming after Gavin.” He says. Which is true. This entire scenario is entirely un-fucking-believable. He couldn’t make it up if he tried.

“Right. Completely, totally outside the realm of possibility.” Ryan says, clear that he doesn’t believe him.

“Even if it was him, I’m sure he’d at least let me know.” Also true. He’s one hundred percent sure, because it has literally happened. He’s not going to tell Ryan that part though.

“Uh-huh.” Ryan says, and Michael has to resist the urge to scream. “Remind me how you heard about all of this in the first place?”

“Same way I hear about everything in this city.” Michael says. “Grapevine.”

“Of course, yeah. See,” Ryan says, head cocked, “that’s the weird thing. It took awhile for me to find someone who had even _heard_ about this hit on Gav. Awfully convenient that you happened to stumble across it.”

“What can I say, Ryan?” Michael stands again, done with this entire conversation. He meets Ryan’s eyes, behind the mask. “I’m a lucky guy.” He says, almost daring Ryan to challenge him on it.

Ryan steps forward. “I hope you know what you’re doing, Michael.” he shakes his head. “I hope it doesn’t get both of you killed.”

“Like Gavin said; if you do your job correctly, it won’t be a problem.”

Ryan holds his gaze for a moment, two. Waiting for him to back down, tell the truth.

He’s going to wait all night. Michael is determined.

“Alright then.” Ryan steps back, clearly dismissing him.

Michael turns and heads back to bed without another word.


	3. Chapter 3

Jeremy calls Matt Bragg the following day.

“Hey buddy! How ya’ been?” he says cheerfully. Matt has been his go-to for years now. He knows tracking Gavin Free down won’t make his ‘Top Ten Easiest Jobs’ list, not by a long shot. Nobody can blame him for enlisting the best hacker he knows. Save for Gavin himself, of course.

“ _What is it now_?” Matt says instead of saying ‘hi’, you know, like a normal friend would.

“Can’t a guy just call his friend to say hello?” Jeremy asks, glancing up towards the window he knows is Matt’s. He’s in an alley across the street, having decided that giving Matt a proper head’s up was low on his To-Do list. He’ll get the ok to come up, do so, and get what he’s come for.

It’s a pretty fool proof plan

“ _I’m sure some people can, but I don’t think it’s something you’re capable of_.” He doesn’t sound mad, per se, just already over Jeremy’s shit. Which, to be fair, he probably has every right to be.

Still. Jeremy’s not about to let him know that. Or let up, for that matter.

“Matt Bragg. I’m hurt that you’d think I’d only call you for a favor.” he says, voice all sing song and too falsely sweet. “I just wanted to check in, see how you’ve been doing.” He pauses, waiting for Matt’s inevitable call of bullshit. When it doesn’t come, he piles on. "You know, like a real friend does? Matt, you never _call_ anymore. I miss you, man.” Which isn’t a lie, exactly, it’s just so off from his actual reason for calling.

“ _Right. If memory serves, the last time we talked was because you needed help tracking down a target._ ” He hears Matt cough away from the mic. Classic Matt Bragg. “ _You’re really tellin’ me history ain’t repeating itself here_?”

“Of _course_ not, man. I just wanna know how you’re doing.” Jeremy says, rolling his eyes. Matt can’t see him, but it makes him feel marginally better.

“ _I- well- I’m good, actually_?” Matt says, sounding confused by Jeremy’s apparent sincerity. Not quite believing it, but accepting it for the moment. “ _I, uh, I hired someone to help me out, and_ -”

“Dude that’s _great,_ really.” Jeremy cuts him off, because this had very quickly become his plan. “Listen, it still stings a little that you didn’t trust me, but it’s fine. I know how you can make it up to me.”

“ _God_ damnit _, Jeremy_!”

“With all your new found help there, you can help me find somebody.” He takes a cursory glance around before heading across the street.

“ _I_ fucking _hate you so much._ ” Matt says, but there’s no real venom to his words. He still just sounds exhausted, like he regrets ever meeting Jeremy.

Good. That’s what he was going for.

He leans on the buzzer for Matt’s apartment. “Hey, let me up.” They’re still on the phone, and he hears his own voice echo through the apartment.

“ _Go fuck yourself.”_ comes the response, both in his ear and crackling through the speaker. But Jeremy hears the click of the door, despite his words.

“You’re the best, Matt.” He says, and hangs up, not giving Matt a chance to retort. He takes the stairs, because the building is old as fuck and he’s never been a fan of elevators anyway. Plus, he knows it’ll piss Matt off even more, which has always been one of life’s little pleasures for him.

He’s known Matt for going on ten years, and he’s spent almost all of them doing everything in his power to annoy him. Matt always falls for his shit, always gives him exactly the reaction he’s going for. In fairness, Matt gives as good as he gets, and if they had a real problem Matt would have made it abundantly clear. They arrived in the city around the same time, found each other early on and formed an easy friendship that has withstood the test of time. They each made names for themselves knowing they had each other's backs every step of the way. In essence, they’d grown up together in Los Santos, and it shows.

He gives Matt the courtesy of knocking, even though he’s sure Matt has already unlocked the door. Confirmed when the door opens immediately.

“Hi Matt!” Jeremy says brightly, a big smile on his face.

“You’re an asshole.” Matt says, immediately turning away from him and walking to his couch. He sits, crossing his arms and leaning back. “Who is it this time?”

“I’m good, too, Matt, thanks for asking.” he says instead of answering, sitting cross legged across from Matt. He’s still all smiles, knowing his chipper attitude will only serve to irritate Matt more.

“You’ve got ten seconds to tell me what you want before I kick you out.”

He should have known what he’d get when he’d started this endeavour. Matt has never been what anyone would call a morning person. To him, 10 am is still too early.

“You’re gonna hate me.”

“I already hate you, so no loss there.”

“So, the thing is… here’s the thing." He's stalling, because he knows this won't go over well. "You know Gavin, yeah? Gavin Free?”

“Yeah?” Matt says, and it’s clear he’s not following.

“Yeah.” Jeremy says slowly, just waiting for it to sink in.

Matt stares at him blankly for another moment before his eyes widen.

“Jeremy, _no._ ” There it is.

“Ok, hear me out. I know. I _know._ ”

“You realize how fucking impossible that is, right?” Matt shakes his head. "There's no fucking way."

"Come on, I believe in you, Matt." He grins. "How often does that happen?"

Matt raises an eyebrow. "For the record, I'm betting that this all goes to shit. But…" he trails off, looking at some point past Jeremy.

"But?" Jeremy prompts, already knowing the answer he'll get.

"But in the event it doesn't, I sure as shit want a cut."

Success.

\---

He spends the day in Matt’s apartment, mostly watching him work. He makes a few phone calls, reaching out to other mutual friends. He doesn’t tell any of them _why_ he’s looking for information on Gavin, just that’s trying to get in touch. To a person, they all tell him to call Michael.

Which. Thanks for that.

"Keep me posted if you find anything." Jeremy says, slipping his leather jacket back on. 

"Right. And when I don't, you'll be the first to know that too." Matt says, crossing his arms.

"Come on. You're the best person I know for this type of shit." He's trying to be encouraging, for once.

Matt chuckles dryly. "I think that speaks to your inability to form meaningful relationships more than it does my skill, but sure." 

"Like you're one to talk."

"I didn't say shit about me." Matt points out. "I know I suck. That's why Fiona does the whole...talking to people thing. She's weirdly good at it." 

"Well thank god for her, I guess."

"Yeah, no shit." Matt clicks around on one of his monitors, looking for something. "It's not much, but I did see security footage of him with Geoff Ramsey. I'll have Fiona go ask around tomorrow, see what she can find out."

"Sounds like a plan. I'll try and figure out who else he knows, if god forbid he's hired any actual protection." He's really hoping that Gavin hasn't. Not that it's ever been a problem for him before, but Gavin clearly has powerful friends. There's a running list of people he doesn't want to be up against in this. 

"Good luck, man." Matt says, leaning back in his chair. "This isn't gonna be an easy one."

 _Oh, you have no idea,_ he thinks.

"Alright, thanks. I'll let you know whatever I find."

He decides to go home, having exhausted his reaching-out quotas for the day. He'd given Michael the warning for a reason. As hard as it will be to actually find Gavin, he doesn't want to push it too hard just yet. He's trying to be as fair about this as possible.

He hopes it wont come back to bite him in the ass.

\---

He wakes up to the sound of footsteps in his apartment. Which is, admittedly, not his favorite way to wake up. He thanks his lucky stars that he’d left his pistol on the nightstand. He tucks it into his waistband, tiptoeing into his living room.

Only to stop immediately short in the hallway.

There, in front of his couch, gun trained, Jeremy knows, right between his eyes, is his worst goddamn nightmare. He reaches back, but he’s met with a dark chuckle.

“I wouldn’t do that if I were you.” The Vagabond says. “It’s rather late, and even I have an itchy trigger finger at this hour.”

“Well. Can’t say I’ve ever wished for a daytime robbery until now.” Despite the warning he’s received, he inches his hand back. If he had just held the fucking gun when he came out, but no, he had assumed it would be something dumb. Thought, maybe, it had been Michael coming to snoop around.

"Careful now." The Vagabond cocks his head. "Wouldn't want me to mistake that" he nods to Jeremy's hand "for you making an incredibly dumb decision. "

“Can’t we at least make this fair?” Jeremy suggests, even though this is The Vagabond and he has approximately zero chance against him. He might be good but The Vagabond is undeniably better.

“If I’d been aiming for fair I wouldn’t have broken in while you were sleeping.” He tilts his head, and Jeremy hears the smile behind the mask. “Would have called you for lunch, maybe.”

“What?”

“I only came to talk, Dooley.”

Which. Alright then. Not only does the fucking Vagabond know who he is, he’s come to Jeremy in the middle of the night to have a chat. That’s not terrifying at all, no.

“Uh. OK?” he says. What else is he supposed to say? No? Right.

The Vagabond sighs. “I suppose you do have a point about making things sporting.” He reaches behind himself, tucking his gun away. He holds his hands out, signalling that they’re empty. “Feel better?” Jeremy takes in the size of his hands, the black gloves, the whole getup, and flat out lies.

“Totally. Relaxed as ever.”

The Vagabond laughs, and the scariest thing about it is how _dorky_ he sounds. It is completely unexpected, and that’s more terrifying than anything. But it does make him actually relax the tiniest bit.

“So. You came to have a talk. What’s up? Birds and bees, or-?”

There’s no laugh this time.

“Rumor has it you’re meant to be after a friend of mine.” The Vagabond says, and Jeremy can hear the upturn in his statement, the smile that accompanies it. Because yeah, that’s a thing to find amusing. “I’d advise against that.” It feels somewhere between a thinly veiled threat and an outright declaration. Like a threat with one string draped across it.

It catches him off guard. “No. No no no, I- I don’t know what you’re talking about.” Because this is the goddamn Vagabond, and while there’s a lot of people Jeremy will go after, someone this literal Bogeyman calls a friend would not be one of them.

The Vagabond tilts his head. “Are you implying I’ve gotten bad information?” A little more veil to it, but christ. Does this guy say anything that doesn’t imply bodily harm?

“No, of course not, I just-” Jeremy smiles weakly. "Can’t imagine anyone willingly going after one of _your_ friends.”

“Mm.” The Vagabond shakes his head. “You’d be surprised, evidently.” He steps forward, and Jeremy squares his shoulders. So this is how it’s going to be. “Well. Whether you know it or not, want to admit it or not- I’ll just leave it at this:” another head tilt, and Jeremy bites back a quip about golden retrievers. “Stay away from Gavin Free.”

In a perfect world, he wouldn’t respond at all. Ideally, he’d act just like he had with the guy who ordered the hit in the first place. He would remain stone faced and act like the name means nothing to him at all. Never heard of the guy, actually. Unfazed, unaffected. However, his life is not like that.

Jeremy’s face falls. How in the fuck had Gavin enlisted the help of the Vagabond in this? No, scratch that, how had _Michael_ done it? That has to be it. Jeremy’s own words float back to him. _May the best man win._ Jesus fucking christ. He’s so entirely screwed.

The Vagabond rocks back on his heels. “So we have an understanding then?”

Jeremy wants to punch the smug smirk off his face. He can’t see it, but he knows it’s there.

“I- I mean, understand what you’re telling me, yeah.”

“And?”

“And-” he cannot believe what he’s about to say. Probably he should just accept defeat and move on with his life. But. “I appreciate the advice. But that’s not exactly sporting, is it?”

“Excuse me?” The Vagabond steps forward again, fully in his space. He doesn’t pull his gun though, so Jeremy doesn't back down.

“What’s that thing they say?” Jeremy raises an eyebrow at him, knowing full well what it is that they say. “May the best man win?”

This close, Jeremy can see past the mask a little, can see startlingly blue eyes staring into his own. Can see them searching, debating. _He’s actually going to say yes to this,_ Jeremy thinks, right before he gets punched in the face.

When he comes to a few minutes later, he’s alone again. He’s still in his apartment, which is a plus. Wicked headache, but he’s had worse. There’s a note scrawled onto a receipt, left unceremoniously on his face.

‘ _I’ll play, but I can’t promise to always play fair.’_

Jeremy wonders, not for the first time this week, what the _fuck_ he has gotten himself into.

\---

He calls Michael the next morning.

“Michael!” Jeremy says cheerfully when he finally picks up.

“ _Jeremy?_ ”

“Couple of questions.” He’s searching through his cabinets, looking for anything that resembles food. “One, what the fuck. Two, _how_ the fuck. And three, _when_ in the actual _fuck_ were you going to tell me you hired the motherfucking _Vagabond_ to protect Gavin?”

“ _Uh. I wasn’t?_ ” Michael answers.

“How the fuck could you do that to me?”

“ _Says the guy planning to kill my boi_ -” Michael pauses. ” _My best friend_.” Jeremy can hear the eye roll in the statement. He can also hear a voice in the background.

“Michael. Who is that?” he asks slowly. He comes across a can of ravioli, and he wrinkles his nose. He’d prefer something better, but it may be his only option.

“ _Um_.” and then, quieter, away from the mic, " _shut_ up."

“Is that Gavin?” There doesn’t seem to be anything else in his kitchen worth eating. He pulls the can of ravioli out.

A pause. “ _Um_.”

“Could you put him on, please?” Jeremy asks him sweetly. This has become such a clusterfuck so quickly. He’s got some choice words for Gavin Free at this point.

“ _Hello_!” comes a lilted voice, far too cheery considering the circumstances.

“Listen here, asshole, I-” but Gavin cuts him off.

“ _So you’re the man who’s been sent to kill me, are you?_ ” Jeremy can hear laughter under the question. Who the hell is this guy?”

He takes a page from Michael’s book. "Uh.” he pauses. "Yeah?”

“ _Well that does put a damper on things, doesn’t it_.” Gavin says with a _tsk,_ like someone finding out they put expired milk in their coffee, not, you know, someone who’s life is in extreme danger.

In the background, he can faintly hear Michael. " _What the fuck is wrong with you?"_

“I guess?”

“ _Right. Well, this whole business is rather...annoying, isn’t it_?”

Jeremy can see why someone would want to kill this asshole. This conversation alone is enough to make him forgo the money and do it out of pure _irritation._

 _“_ Murder tends to be, yeah.” He sets the can on the counter, the ‘ _clack’_ echoing through the apartment.

“ _That goes without saying.”_ Gavin says with a dismissive laugh. “ _But it’s business, I’m afraid.”_

“Right. So-” But Gavin cuts him off. Again. He turns, back against the counter.

“ _See the real problem we have here is,”_ Jeremy is pretty sure the pause is simply for dramatic effect. Asshole. “ _You’re quite a good friend of_ Michael’s, _but the Vagabond happens to be a quite a good friend of_ mine.” Which. Ok, what the fuck? “ _Genuinely, I’d rather not see anything bad happen to either one of you.”_

Fuck. This. Shit. Gavin wants to play this little game on the phone, fine. Jeremy can play. He takes a deep breath.

“You’re aware, I’m sure, that neither the Vagabond or I are the ones with the target on our backs?” The problem is, Jeremy has never been on to play with any subtlety.

“ _Well-_ ” and now it’s his turn to cut Gavin off. It probably shouldn’t feel as good as it does.

“The odds of either of us getting seriously hurt are much lower than they are for you, Gavin.”

“ _Now-_ ” and again. Feels better the second time.

“I was paid to do a job, and I take pride in my work. _Your_ friend may be the scary ghost in the night, but he’s not the only one with a one hundred percent success rate." And then, just for dramatic effect, " _Motherfucker.”_ And he hangs up without another word.

Out of spite or fear, he’s not going to dwell on.

He glances over his shoulder at the can on his counter. He sighs, turning and putting it back up in the cabinet. _Forget it,_ he thinks. 

He’s lost his appetite.


	4. Chapter 4

**Notes for the Chapter:**

> I know it's been a minute, life kinda fucked me for a bit, and then writer's block was a real bitch about it.

Ryan has never been what anyone would call… inconspicuous.

He’s spent almost ten years building a reputation, a persona, a rumored force that borders on inhuman and impossibly scary. He wears a skull mask most times he leaves his house.. He has never been one for tiptoeing around issues, always been one to reach out and take the information he needed.

This whole Gavin situation is entirely different.

He’s ninety percent sure Michael is good friends with the hitman, which is a real clusterfuck, if he’s being honest. It’s only further evidenced by Gavin specifically instructing him to do what he can to _not_ kill him. He’s never known Gavin to really give a shit about anyone else’s life. He cares only if that life may have bearing on his own.

Ryan wants to believe Michael. He does. He wants to believe that the two of them would have more sense than to lie to him about who Dooley really is. He’s just known them for too long to trust that desire.

So, as is his (extremely questionable) habit, he drops by unannounced.

It occurs to him, as he climbs through the spare bedroom window, he could have knocked on the door. The couple would probably prefer it, so he immediately disregards it as an unacceptable option. He lands gracefully onto the bed, the springs squeaking loudly under his ass.

“Shh.” He reprimands, even though they’re literally inanimate objects and he’s the one who had complete control over whether they made a noise.”Please don’t do that.” He whispers, and a moment later he hears distant meowing heading his direction. Damn cat.

A paw swipes under the closed door, and there's the sound of the cat’s head bumping along with it. Ryan shakes his head. Of course Gavin’s cat would be able to play lookout but not actually _do_ anything. He opens the door quietly, careful to avoid running it over the little paw.

He couches down, scratching the cat behind his ears. The cat is still meowing, now intermittent with rumbling purring. “Shh.” he says again. “You’re gonna give me away.”

The cat backs up, looking up at him almost pointedly, like he’s well aware that _Ryan_ is the one trespassing and has no room to reprimand anyone else.

Ryan reaches out again. “I’m sorry.” He whispers. “You’re perfect. You’re right, I’m the asshole.” He sits himself cross legged in the doorway, back against the open door. The cat takes a hesitant step forward before deciding _fuck it,_ apparently, and climbing into Ryan’s lap.

No one would know it by looking at him, all scary skull mask and and leather getup, but he’s a sucker for animals. If it weren’t for his job, he’d be happiest on a farm in the middle of nowhere, just a herd of pets and creatures around him.

He pulls his gloves off and sets them beside himself, seeing the way the cat is still eyeing them warily.

“Is that better?” he asks quietly. “I know, I’m sorry, I wasn’t thinking.” _He_ may never describe it as cooing, but that’s exactly what it is. He wonders what he must look like, if someone were to find him like this. _Masked man breaks in to play with cat- More at 11._

It’s a little ridiculous, he knows. Not that he cares. He’s happy to have this little ball of fluff purring in his arms.

Without warning, the hall light clicks on.

“What the fuck are are you doing?” Comes a voice, and Ryan looks up to find Michael staring at him, hands on his hips.

He feels a bit like a child caught with his hand in the cookie jar, if he’s being honest. ”Uh.” he says, not quite sure how to explain. He glances down at the cat in his arms, who’s being a real asshole and looking at Michael like he doesn’t know how on earth he’d ended up here. “This is your fault.” He says matter-of-factly, and immediately the cat is jumping from his lap. The cat skitters past Michael and into the bedroom, no doubt heading straight for Gavin.

Ryan looks up at michael. “So I came to talk.” he says, hoping to bypass any explaining he might have to do. He’s still on the floor.

Michael rolls his eyes. “To us or the goddamn cat?” He asks sarcastically. He turns and waves Ryan forward. “Come on. I’m sure Gav is chomping at the bit to hear whatever this is gonna be.”

Ryan laughs, but gets up to follow him anyway.

“So. Any updates?” Ryan asks, stepping into the bedroom. Gavin has the traitorous cat sitting on his chest, and a smile on his face. Michael is beside him, arms crossed and looking far less pleased with the situation.

“Isn’t that supposed to be your job?” Michael says shortly.

“He’s got a point, Ry.” Gavin says, not looking up from the cat. “Also, mask.”

Ryan sighs, but dutifully pulls the mask off. He tosses it a little too forcefully at Michael, who immediately bats it away and onto the floor.

“You haven’t seen or heard anything unusual?” And that’s mostly directed at Michael, because Ryan is so sure he knows something.

“Besides some masked moron breaking into our guest bedroom?” Michael asks, eyebrows raised. “Not a thing.”

“Very funny.” Ryan rolls his eyes. “You’re sure?” He sits on the foot of the bed, and Michael makes a disapproving noise. “No weird sounds or knocks at the door?”

“Ryan, if we had something to tell you we would.” Gavin says. He pulls the cat closer, pressing his face against the cat’s head.

“Why don’t I believe that?” Ryan asks, shaking his head.

“Because you’re a cagey bastard with trust issues.” Michael says matter of factly. “And you think the worst of everyone.”

Ryan raises an eyebrow. He’s not wrong. “Fair play.”

“You’re damn right that’s fair.” Gavin finally looks up from the cat and grins at Ryan. “But we wouldn’t have you any other way.”

“No, I could do without the breaking and entering.” Michael leans over and pulls the cat from Gavin’s grasp, sitting him in his lap. “And you showing up like a creep in the middle of the night. And the mask.” He nods toward the floor. “And your overall demeanor.”

“Anything else?” Ryan asks. It’s all in good fun, for the most part.

“Uh.” Michael thinks for a moment, rubbing the cat against his face. “If you could work on literally everything else about you, that would be great.”

Ryan chuckles drily. “Thanks so much. I’ll keep it in mind.” He shakes his head, getting up from the bed. “You two are useless.” He leans down and picks his mask back up. He fits it back onto his head, fixing Michael with a glare. “ _Useless.”_ He tries to muster as much venom as he can.

“Oh, Gav, Ryan’s cranky now.” Michael says with a snicker. Apparently venom hadn’t worked.

“Alright, I have other stops to make this evening.” Ryan says, even though he really doesn’t. He’ll figure something out. He steps forward, giving the cat one more scratch behind the ears before he turns to leave.

“Feel free to use the front door for once." Gavin says with a smile.

Ryan pauses and sighs, deep and exhausted, but doesn't look back. He shakes his head and continues on his way. He might as well take the advice, he doesn't particularly feel like climbing back out of the window.

Before he's gone, though, he gets stopped.

“Hey, Ryan, in all seriousness, thanks for looking out.” Michael says. He's followed Ryan to the living room, having chosen to have this conversation out of earshot of Gavin. Interesting.

Ryan turns to him, hand on the doorknob. "You're not the only one who cares about him, Michael." That's why this job is so different from others. Gavin is, above all, one of his closest friends. He can't let it end badly.

"I-" Michael pauses, takes a breath. "Yeah, I know." He clears his throat loudly, clearly uncomfortable with the interaction. "Listen, get some sleep, will you? I can keep an eye on him tomorrow night."

"Michael-"

"I'm serious." He says, time firm. "I know you. You're worried. So am I, but you're no good to him if you're dead on your feet." Ryan wouldn't call it pouting, per se, but he does pull a face. Even though Michael can't see it. "Don't pout at me, you child. I'm right."

" _Fine._ " He concedes. "If you think you've got it here." He's already plotting other ways to spend the time, who he can reach out to for assistance.

"Stay in your goddamn apartment and sleep, or I'll fire you myself." As if he knows what Ryan is thinking. They really have been friends for too long.

"You're not the one who hired me, Gavin is, and Gavin-" Ryan starts.

"Will _absolutely_ fire you for a laugh. Especially if I tell him to." And the thing is, he's right. One of the many irritating traits that Gavin has.

"God, fine. I'll stay home like a good dog, ok?" He holds up his hands in mock surrender. "Happy now?"

"Thrilled." Michael says with a smile. He turns to head back to bed. "Stay safe, Ryan." He adds, seemingly as an afterthought. He disappears down the hall before Ryan can return the sentiment.

\---

Once he's outside, he tries to figure out where to go. He hasn't had any other stops planned, had been content to lurk around the building for the rest of the evening. But knowing Michael, he'll be checking around just to prove a point.

He considers calling Geoff. If he needs resources, Geoff is the best one to lean on. He doesn’t need to, really, because they’re isn’t anything _happening_ with the whole hitman situation. As far as he’s been told, Gavin and Michael haven’t heard anything new, and he hasn’t seen any unusual activity around the apartment. With the whole ‘try not to kill/ seriously injure Jeremy’ rule Gavin had put in place, he doesn’t have much to do besides wait.

He’s getting antsy, though, especially at night. So he goes to Geoff. It’s not that he _needs_ advice, he’s just curious what Geoff may have to offer. That’s it.

He finds himself on the fire escape before he remembers the spare key Geoff had given him months ago. Oh. He tries the window anyway, hoping now that it won’t open.

It does.

Well then. He slides the window all the way open. Serves Geoff right for not checking his windows before bed. It’s a dangerous city, and he’s goddamn lucky Ryan is the one doing the breaking and entering. Could be so much worse. He climbs through in a totally skilled and graceful way, and most certainly doesn’t just fall through the window and get the wind knocked out of him.

Not at all.

Geoff finds him on the floor on his back, still trying to catch his breath.

“What the fuck is wrong with you?”

Geoff is behind him. He looks up and holds up one finger, asking for just a moment.

“I gave you a goddamned key so you would _stop_ this shit, Ryan.” Geoff says, crossing his arms. He doesn’t seem _genuinely_ annoyed, just a little perplexed.

“You should lock your windows at night, Geoff.” Ryan says finally. Geoff grimaces at the mask.

“I should take back that fuckin’ key.” Geoff says, shaking his head. “Not like you’re using it anyway.”

Ryan holds up an arm. “Little help?”

Geoff rolls his eyes, but steps forward, pulling Ryan up easily. He lets go with a little shove, and Ryan stumbles backward into the couch.

“ _Geoff._ ”

“Serves you right.” Geoff says with a shrug. He steps to the window, glancing down quickly before sliding it closed. He flips the lock with a pointed look at Ryan. “Happy now?” He sits back in the recliner, pulling one leg up. His other foot is bouncing on the carpet.

“Listen. I’m really just concerned for your safety, Geoff. I did you a favor, really.” Ryan pulls the mask off and grins at him. He knows he looks more terrifying without the mask, all smeared face paint and wild eyes.

“Gross, dude.” Geoff says with a frown. Whether because of the facepaint or the concern, Ryan doesn’t know. “Did you actually _want_ something from me? Jack’s gonna be pissed if she wakes up.”

“ _No bullshit after 10 pm._ ” Ryan recites the text he’d received from Jack on multiple occasions. “I know. But she owns a bar. Shouldn’t she be used to it?”

“She’s off tonight. Was real excited to be able to relax for one night.” Geoff informs him. “So was I, by the way. What do you want?”

So Geoff isn’t playing games tonight. Alright, fine. Ryan can be honest when he needs to be.

“Has Gavin told you what’s going on?” The upside is maybe he can make Geoff feel like an asshole. One of life’s little pleasures.

Geoff sighs, long and exhausted sounding. He studies Ryan for a moment, who squirms under the scrutiny. He didn’t come here to be analyzed. “Yeah.” Geoff says after a minute. “Yeah, I heard.”

It doesn’t escape Ryan that there’s worry in his eyes. “What do you think?”

Geoff chuckles, dry and humorless. “What do I think? I think it was bound to happen eventually. Kid’s a prick. I’ve lost count of the number of times I’ve wanted to kill him myself.” Geoff smiles, but it’s strained.

All of them are good at the humor-as-a-coping-mechanism thing. Not so much at the actually-coping.

“Have you heard anything about the hitman?” Ryan asks. Might as well go for gusto.

“Dooley, or something, yeah?” Ryan nods. “Talented guy. I’ve looked into hiring him a few times. Never lined up though.” Geoff shakes his head. “It’ll be a shame to see him go.” He says with a look to Ryan. Of course.

“Gavin is adamant that I don’t hurt the guy, just stop him.” Ryan says. He’s still not sure how he feels about that one.

“Gavin’s a fucking idiot.”

Yeah, that about sums it up.

“Believe me, I know.” He shrugs. “But it’s up to him. His money.”

“There’s no way that’s gonna work out well for him.” Geoff says, frowning. “Right?”

"I don't see a scenario in which it does, no." Ryan says honestly. He's been thinking it through ever since Gavin made the request, and it still doesn't make sense. Someone has to die at the end of this. There's no way around it. 

"You're a better man than me, Ryan." Geoff says, shaking his head. "I would've put the guy down the second I had the chance."

Ryan purses his lips. "Better might be a strong word, Geoff." He chuckles humorlessly. "Dumber, maybe." 

"Nah." Geoff shoots him a grin. "You're a good guy, Ryan. If I wasn't already married…" he trails off with a wink.

"We can fix that." Comes a new voice, and Ryan looks to the door to find Jack standing there, hands on her hips.

"Hi, Jack!" Ryan says cheerfully.

Jack does not look as happy to see him.

" _No bullshit after 10 pm_ ." She says, tone sounding very much like she's scolding a child. "It is the _only_ rule I have, and yet here you are." She gestures vaguely at him. "Geoff, why did you let him in?"

"He, uh. He climbed in through the window?" Geoff admits quietly.

"Goddamnit Ryan!" Jack crossed her arms tightly, leaning on the door frame.

"I have a good reason for being here." Ryan says. Geoff has begun giggling from his recliner, evidently happy that Jack's irritation is no longer directed at him.

"I sincerely doubt that." Jack starts tapping one slippered toe on the carpet.

"There's a hit out on Gavin." Ryan blurts out. Truthfully, she scares him. One of the only people who can.

"I'm aware." She says flatly. "There's gonna be a hit on you if you don't stop with your bullshit after 10." Despite her words, her face softens a bit. "How's he doing?"

"He doesn't seem to be worried." Ryan says truthfully. He's still deeply confused by that one. Maybe he has more faith in Ryan than he'd realized.

Jack shakes her head, laughing quietly. "He's Gavin. He's never worried a day in his life, even when he should have." She studies Ryan for a moment, then sighs. "I shouldn't sign up for this, but if you need anything, don't hesitate to ask." she glances at Geoff. "Or- don't hesitate to ask him. I'm going back to bed." 

"Don't involve me in this!" Geoff says quickly. He scrambles up and moves toward Jack, almost like he's trying to hide behind her. 

"I should probably go, anyway." Ryan says, standing. He's gotten what he'd come for- confirmation that Gavin's request was as weird as he thought, and assistance if he needs it. He's already considering how to cash in that offer of help. He grabs his mask and moves towards the couple. "I appreciate it, Jack. I have a feeling I'm going to be needing the help." 

"Please be careful." Jack says, and now that Ryan is closer he can see the worry in her eyes too.

"It'll work out." He says, far more confidently than he feels. He pauses to politely kiss her on the cheek, and laughs when Geoff looks vaguely offended. "Problem, Geoff?"

"Jack gets a goodnight kiss but I don't?" He says, shaking his head. "That's bullshit."

Ryan chuckles, but gives him the same quick peck on the cheek. "Feel better?"

"Not in the slightest." Geoff says, rubbing away the transfer of the face paint. "Now get the fuck out."

Ryan does, via the actual door for the second time this night. He heads back to Gavin's place. It's nearing 3 am, so he highly doubts there will be anything to keep an eye on, but still. It makes him feel better.He trusts that Michael will be a man of his word and play lookout tomorrow. He also knows that if he tries to swing by, he'll end up with a lecture. Might as well make the most of the night he _does_ have. 

There isn't much to see, and he mostly hangs out in an alley across the street. At least its marginally better than sitting in his apartment, alone.

\---

At about 2 am the next night, Ryan decides there’s no way he’s going to get any sleep. Michael had been so adamant about not needing a lookout, Ryan can take the night off. Which. He’s not thrilled about it, but if Michael thinks he can really handle it, fine. He’ll let it happen.

This whole thing with Gavin is weighing entirely too heavily on his mind. He still can’t imagine how the fuck it’s supposed to end. Gavin had explicitly instructed him not to bring harm to Dooley, and technically Gavin did hire him. So it’s not like he can refuse. But God, what’s he even doing then? If it comes down to Dooley’s life or Gavin’s, he can’t exactly honor that promise.

How does this end?

At 2:15 he thinks ‘fuck it’ and gets up. He won’t get dressed, won’t go out and lurk in the shadows, but still. He can surely eat some ice cream. That should fix his woes, right? And it would, probably, if he goddamn had any.

He figures he can risk one light night adventure without the Vagabond get-up. It hasn’t gone over well in the past, and he’s truly not trying to fuck with anybody. He just wants some ice cream. He throws on a pair of jeans and hoodie, not entirely comfortable with heading out in pajama pants. He hooks a knife to his belt loop, just in case, and yanks the hoodie down over it.

Good enough.

It’s a short walk to his neighborhood convenience store. The convenience being that they’re open at 2:30 in the morning, _and_ they carry his favorite flavor of ice cream. The total package, really. It’s not a big place, a handful of aisles and a bored cashier. He turns the corner to the cold case, and finds what he least expects.

Jeremy fucking Dooley, in sweatpants and a tanktop. He’s wearing what appear to be house slippers, for chrissake. He’s got one hand on the freezer door, a six pack of beer in the other, and he’s squinting at the freezer like he doesn’t trust it.

Ryan stops dead in his tracks. He can’t help but stare at the man, so out of place in here, a store Ryan is so familiar with. It doesn’t quite compute. 

There’s also the matter of Ryan noticing things he hadn’t before. Namely, muscles. In Dooley’s apartment, he’d been in work-mode. All sinister, imposing threats, focusing on the task at hand.

Here? Here he’s just Ryan, and Ryan is impossibly distracted by things like the small strip of skin between the bottom of Dooley’s wife beater and the top of his sweatpants.

He only has another moment to openly stare before Dooley turns and notices him. Dooley smiles at him sheepishly, whatever irritation had been in his expression is now gone. “Sorry, man. Am I in your way?”

Ryan- well he flat out panics. He can’t _answer_ , because he knows he’s got a pretty distinct voice. They’d only ever had the one conversation, but still. There are news clips out there from before, from the days he played offense instead of defense. Shouting in the middle of heists, a few colorful messages he’d left for various politicians. His voice is easily recognizable, and if Dooley is half as good as everyone seems to think he is, he’ll zero in on it immediately.

So.

“Nope!” He tries to pitch his voice higher, putting on a terrible British accent. It sounds ridiculous to his own ears, and Dooley’s surprise is written on his face. “Not at all!” The accent somehow morphs into vaguely Australian, and Ryan kind of wants to die.

“Uh, alright.” Dooley steps back anway, turning to the case again.

Ryan turns his attention to the case as well, not that he’s actually seeing any of the ice cream. He’s too busy trying to quell the myriad of thoughts in his head. There’s nothing he can do or say here that’s going to help any. If he grabs a pint of ice cream, he still has to checkout, has to say something to the cashier. He’s too committed to the fake voice by this point, and that’s not a route he’s willing to go down. If he leaves, he’s some weirdo who walked up to a guy, stared at him and then walked away. That’s not suspicious, not at all. Plus, no ice cream.

No, he has to stand here next to his technical _rival_ , and wait until he’s done. That is his only option.

Dooley turns to him again. “I don’t mean to be that guy who talks to strangers at the grocery store, but man, I hate when they stop carrying shit.” Dooley shakes his head. “Used to come here all the time for Cherry Garcia. Now it’s gone and there’s too many options. Shit sucks.”

Ryan nods, a little too enthusiastically. “Terrible!” he says, also a little too loudly. “The worst!” His fake accent is what’s actually getting worse, morphing into the worst Gavin-impression that’s ever been done.

“Any recommendations, dude? I’ve spent the last like, six years eating exclusively Cherry Garcia.”

“It suits you.” The horrifically accented words are out of his mouth before he can process them. He’s _mortified,_ and Dooley raises an eyebrow.

“Uh, thanks? I think?” he looks down self consciously.

“Here.” Ryan steps forward and grabs two pints of some cake batter monstrosity. He’s never actually had it, but it’s the closest. He needs this moment to be over as soon as possible. “We’ll both try something new!” he shoves one pint into Dooley’s hand, and holds up the other. “We match.”

Dooley laughs. “Yeah, I- I guess we do.” He smiles, and gives Ryan a very obvious once-over. “Hey, would you maybe wanna-” he gestures vaguely toward the door, and Ryan’s brain short-circuits.

“I have to go.” he says loudly. “Need bread.” he follows up, as if the bread isn’t directly behind Dooley.

“But it’s-”

Ryan walks away. He doesn’t even grab a loaf of bread, even though he kind of did need it. Nothing good can come of this. He has to leave right now, immediately, or everything is going to fall apart. He can’t keep up the accent any longer, and if he uses his real voice Dooley will _know._ So he throws a ten dollar bill on the counter and walks out.

“Sorry!” he can faintly hear Dooley call. “Bye!”

Ryan all but runs back to his apartment, not even considering that Dooley could follow him. He tosses the (now extremely expensive) ice cream in his freezer, and heads back to bed. He doesn’t change out of the jeans, just lays face down on his comforter. Never before has he faced such a disaster in the name of dessert. 

Looming badass, he can do. Threats and murder and chaos, he’s got. He’s had years of practice being scary, being a force to be reckoned with. He’s taken down countless enemies, negotiated hundreds of deals. He can do it all without thinking. Stumbling upon his enemy in a grocery store _and_ realizing that enemy is ridiculously attractive? Not so much.

What the _fuck._

**Notes for the Chapter:**

> Ryan is a dork, y'all. And we love him for it.


End file.
